2-(Di-tert-butylphosphino)biphenyl → (S)-2-sec-butylamino-6-methanesulfonylamino-isonicotinic acid methyl ester

HRID 1436494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436494
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40].[Na]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([NH:42][S:39]([CH3:38])(=[O:41])=[O:40])[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1

Komponenten

6

Edukt 3

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 86614996HCID 86614996, VerbindungHCID 86614997HCID 86614997, Verbindung

Produkt 1

HCID 68814626(S)-2-sec-butylamino-6-methanesulfonylamino-isonicotinic acid methyl esterAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
99 °C

Versuchsvorschrift

Add to a 300 mL of autoclave reactor (s)-(+)-2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (12.46 g, 0.05134 mol), bis(dibenzylideneacetone)palladium (0) (2.35 g, 0.002567 mol), 2-di-tert-butylphosphino biphenyl (1.53 g, 0.005134 mol) and sodium methanesulfonamide (12.02 g, 0.1027 mol) in toluene (250 mL). Flush with nitrogen 3 times and heat to 99° C. for 24 h. Filter and dissolve the filter cake in water (400 mL). Extract the aqueous layer with chloroform (3×200 mL), dry (magnesium sulfate) and concentrate. Dissolve the crude product in dichloromethane (20 mL) and precipitate out by adding hexanes (400 mL) to give a solid (7.18 g, 46%).

Aufarbeitung

  1. customFlush with nitrogen 3 times
  2. filtrationFilter
  3. dissolutiondissolve the filter cake in water (400 mL)
  4. extractionExtract the aqueous layer with chloroform (3×200 mL)
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. dissolutionDissolve the crude product in dichloromethane (20 mL)
  8. customprecipitate out
  9. additionby adding hexanes (400 mL)

Quellen und Nachweise

ORD-Eintrag
ord-16481f15470d4567aa98b5cc2a46fb3f
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618978B2

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